Process for obtaining N-monosubstituted amides

Abstract

A process for obtaining an amide of the general formula R-(CO)—NH—CH 2 —X involves contacting a nitrile of the general formula R-CN with: a) an acid; and c) an alkoxy-containing compound comprising at least one alkoxy functionality of the general formula —OCH 2 -X; wherein R is hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, which substituents can be substituted or unsubstituted; wherein X is hydrogen or a radical having the general formula —CHR 1 R 2 ; and wherein R 1 and R 2 independently or collectively represent hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, or any combination thereof, which substituents can be substituted or unsubstituted. Moreover, the inventive process can involve other similar reactions, for example, at least one nitrile can be reacted with a reagent comprising both (i) at least one suitable alkoxy functionality; and (ii) at least one suitable acid functionality.

What is claimed is:  
     
         1 . A process for obtaining an amide of the general formula:  
       R-(CO)—NH—CH 2 -X  comprising contacting a nitrile of the general formula:    R-CN    with a monoalkylsulfate of the general formula:    XCH 2 OSO 3 H,    wherein:    R is hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocycle, which substituents are substituted or unsubstituted, and X is hydrogen or a radical having the general formula —CHR 1 R 2  wherein R 1  and R 2  individually or collectively represent hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, or any combination thereof, and which substituents are substituted or unsubstituted.    
     
     
         2 . The process of  claim 1  wherein R is substituted with a functional substituent.  
     
     
         3 . The process of  claim 1  wherein X is substituted with a functional substituent.  
     
     
         4 . The process of  claim 1  wherein the monoalkylsulfate is monomethylsulfate, monoethylsulfate, monopropylsulfate, or monobutylsulfate.  
     
     
         5 . The process of  claim 1  wherein nitrile is added to monoalkylsulfate.  
     
     
         6 . The process of  claim 1  wherein the monoalkylsulfate is added to nitrile.  
     
     
         7 . The process of  claim 1  wherein the monoalkylsulfate and nitrile are fed simulataneously into a reactor environment.  
     
     
         8 . The process of  claim 1  comprising the step of forming the monoalkylsulfate from the reaction of: 
 a) an acid; and  
 b) an alkoxy-containing compound comprising at least one alkoxy functionality of the general formula:  
 —OCH 2 -X  
 wherein:  
 X is a radical having the general formula —CHR 1 R 2  wherein R 1  and R 2  individually or collectively represent hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, or any combination thereof, and which substituents are substituted or unsubstituted.  
 
     
     
         9 . The process of  claim 8  wherein the acid is sulfuric acid or fuming sulfuric acid, and the alkoxy-containing compound is an alcohol, a dialkyl sulfate, a trialkyl borate, a trialkyl phosphate, an alkylorthosilicate, an alkylorthotitanate, an alkylorthocarbonate, a dialkylcarbonate, a dialkylacetal, a dialkylketal, a dialkyl ether, a glycol ether, an arylalkyl ether, or an alkyl ester.  
     
     
         10 . The process of  claim 8  wherein the acid is chlorosulfonic acid, sulfur trioxide, or complexes of sulfur trioxide, and the alkoxy-containing compound is an alcohol.  
     
     
         11 . The process of  claim 8  wherein the monoalkylsulfate forms in situ.  
     
     
         12 . The process of  claim 1  wherein the nitrile is acetonitrile, propionitrile, 2,3-dimethyl-2-(1′-methylethyl)butanenitrile, p-menthanecarbonitrile, or benzonitrile.  
     
     
         13 . The process of  claim 1  wherein the molar ratio of monoalkylsulfate to nitrile is from about 0.1 to about 50, and the contacting is carried out at a temperature from about minus 20° C. to about plus 250° C.  
     
     
         14 . The process of  claim 1  wherein the molar ratio of monoalkylsulfate to nitrile is from about 1 to about 5, and the contacting is carried out at a temperature from about plus 25° C. to about plus 180° C.  
     
     
         15 . The process of  claim 1  performed in the presence of an organic or inorganic solvent.  
     
     
         16 . The process of  claim 1  wherein monoalkylsulfate is added to nitrile.  
     
     
         17 . The process of  claim 1  wherein the nitrile is added to monoalkylsulfate.  
     
     
         18 . The process of  claim 1  wherein the nitrile and the monoalkylsulfate are simultaneously added to a reactor environment.  
     
     
         19 . The process of  claim 1  which process is performed batch-wise.  
     
     
         20 . The process of  claim 1  which process is performed continuously.